83781-92-4

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 57754-01-5 2-[(trimethylsilyl)methyl]benzyl alcohol 
• 34599-77-4 (E)-1-methyl-2-(penta-2,4-dien-2-yl)benzene 
• 82902-64-5 (E)-1-(but-2-en-2-yl)-2-methylbenzene 
• 134261-82-8 1-Methyl-2-(1-methylene-but-3-enyl)-benzene 
• 82902-62-3 2-(2-methylphenyl)but-1-ene 
• 83845-46-9 1-Methyl-2-(1-methylene-hex-5-enyl)-benzene 
• 104330-78-1 2-(trimethylsilylmethyl)benzyl bromide 
• 155203-56-8 Trimethyl-[2-(toluene-4-sulfonylmethyl)-benzyl]-silane 
• 160929-76-0 Trimethyl-{2-[1-(toluene-4-sulfonyl)-ethyl]-benzyl}-silane 
• 160929-77-1 Trimethyl-{2-[1-(toluene-4-sulfonyl)-but-3-enyl]-benzyl}-silane 
• 160929-87-3 Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-but-3-enyl]-benzyl}-silane 
• 160929-79-3 Trimethyl-{2-[2-methyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-silane 
• 160929-85-1 Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-silane 
• 160929-89-5 {2-[1,2-Dimethyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-trimethyl-silane 

Relevant academic research and scientific papers

Synthesis and Conversions of Substituted o-[(Trimethylsilyl)methyl]benzyl p-Tolyl Sulfones to o-Quinodimethanes and Products Thereof

Use of o-[(trimethylsilyl)methyl]benzyl p-tolyl sulfone (3) for synthesis and cycloaddition of substituted o-quinodimethanes has been investigated. Sulfone 3 is prepared from 2-methylbenzyl alcohol (4) by reactions with n-BuLi and chlorotrimethylsilane to form o-[(trimethylsilyl)methyl]-benzyl alcohol (7) which phosphorus tribromide converts to o-[(trimethylsilyl)methyl]benzyl bromide (8). Displacement of 8 with sodium p-toluenesulfinate yields 3. Sulfone 3 is alkylated at its α-sulfonyl position upon deprotonation with n-BuLi followed by methyl iodide, ethyl, butyl, allyl, and benzyl bromides, and 5-bromo-1-pentene, respectively. Acylations occur using acid chlorides. Dialkylation occurs upon further reaction with n-BuLi and an alkyl halide. 1,4-Eliminations of α,α-dialkyl sulfones 11 with tetrabutylammonium fluoride (TBAF) give α,α-dialkyl-o-quinodimethanes (29); 3 is therefore a synthon for the o-quinodimethane-α,α-dianion (34). o-Quinodimethanes 29 undergo (1) cycloaddition with acrylonitrile, acrylate esters, and alkyl fumarates to yield 1,1-disubstituted-tetrahydronaphthalenes (30) and (2) 1,5-sigmatropic rear-rangements of hydrogen to give styrenes (32). The stereochemistries of the various cycloadditions reveal significant mechanism information.

DIRADICAL CYCLIZATION METHODOLOGIES. MODEL STUDIES PROBING THE APPLICATION OF PHOTOINDUCED-ELECTRON TRANSFER PROCESSES IN SYNTHETIC ROUTES TO THE PROTOBERBERINE AND SPIROBENZYL ISOQUINOLINE ALKALOIDS

Model studies have demonstrated that diradical cyclization processes, promoted by excited state electron transfer-desilylation pathways, serve as novel methods for construction of ring systems found in members of the protoberberine and spirobenzyl isoquin